Photoredox-catalyzed multicomponent transformation towards functionalized <i>trans</i> -2,3-disubstituted indolines

We report a visible light photoredox-catalyzed multi-component reaction (MCR) of <i>N</i>-substituted 2-vinyl anilines, diaryliodonium triflates, and sulfonium/sulfoxonium ylides for the efficient synthesis of a diverse range of functionalized <i>trans</i>-2,3-disubstituted indolines in good to excellent yields. While the MCR involving sulfonium ylides is catalyzed by Ru(bpy)<sub>3</sub>Cl<sub>2</sub>·6H<sub>2</sub>O, the MCR with sulfoxonium ylides can be carried out using inexpensive organic dye fluorescein. Control experiments unequivocally establish the intermediacy of radicals derived from both diaryliodonium triflates and sulfonium/sulfoxonium ylides. The redox-neutral process displays a broad substrate scope, high structural diversity, and proceeds under amenable conditions.

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Publication Details

Journal
Chemical Communications
Published
2025-11-28
DOI
https://doi.org/10.1039/d5cc06032j
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photoredox-catalyzed multicomponent transformation towards functionalized trans -2,3-disubstituted indolines

Prahallad Meher, Suresh Chandra, Sandip Murarka, M. Siva Prasad
Chemical Communications
Radical Photochemical Reactions
article

Photoredox-catalyzed multicomponent transformation towards functionalized trans -2,3-disubstituted indolines

Prahallad Meher, Suresh Chandra, Sandip Murarka, M. Siva Prasad
article en

Abstract

We report a visible light photoredox-catalyzed multi-component reaction (MCR) of <i>N</i>-substituted 2-vinyl anilines, diaryliodonium triflates, and sulfonium/sulfoxonium ylides for the efficient synthesis of a diverse range of functionalized <i>trans</i>-2,3-disubstituted indolines in good to excellent yields. While the MCR involving sulfonium ylides is catalyzed by Ru(bpy)<sub>3</sub>Cl<sub>2</sub>·6H<sub>2</sub>O, the MCR with sulfoxonium ylides can be carried out using inexpensive organic dye fluorescein. Control experiments unequivocally establish the intermediacy of radicals derived from both diaryliodonium triflates and sulfonium/sulfoxonium ylides. The redox-neutral process displays a broad substrate scope, high structural diversity, and proceeds under amenable conditions.

Chemical CommunicationsVol. 62(2)
Indian Institute of Technology Jodhpur (IN)
Openalex Percentile: Top 72%
Radical Photochemical Reactions
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